JPWO2010013676A1 - Organic light-emitting medium and organic EL device - Google Patents

Abstract

An organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (2).

Description

  The present invention relates to an organic light emitting medium and an organic EL device using the same.

  Conventionally, an organic EL element (organic electroluminescent element) using light emission of an organic compound is known. The organic EL element has a plurality of organic thin films stacked between an anode and a cathode. In this configuration, when a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively. Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.

As an example of the material used for the light emitting layer, Patent Document 1 discloses a combination of an anthracene host and an arylamine. Patent Documents 2 to 4 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant. Furthermore, Patent Documents 5 and 6 disclose anthracene-based host materials.
However, any of the materials has a problem that it is difficult to obtain high luminous efficiency and the life is short.

WO 2004/018588 WO2004 / 018587 JP 2004-204238 A WO2005 / 108348 publication WO2005 / 054162 publication WO2005 / 061656

  INDUSTRIAL APPLICABILITY The present invention is capable of obtaining high luminous efficiency, has a long lifetime, an organic EL element including a combination of a specific host material and a dopant material, and an organic light emitting medium that can be used for an organic thin film layer of the organic EL element The purpose is to provide.

（式（１）中、Ａｒ^１〜Ａｒ^４は、それぞれ独立に、置換もしくは無置換の核炭素数５〜５０のアリール基又は置換もしくは無置換の核炭素数５〜５０の複素環基である。
Ｒ^２１〜Ｒ^２４は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数５〜５０のアリール基、置換もしくは無置換の核炭素数６〜５０のアラルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数５〜５０のアリールオキシ基、置換もしくは無置換の核炭素数５〜５０のアリールアミノ基、置換もしくは無置換の炭素数１〜２０のアルキルアミノ基、置換もしくは無置換の核炭素数５〜５０の複素環基、置換もしくは無置換のシリル基、シアノ基又はハロゲン原子である。
ｎ１〜ｎ４は、それぞれ独立に、０〜５の整数であり、ｎ１〜ｎ４のそれぞれが２以上の場合、Ｒ^２１〜Ｒ^２４は、それぞれ同一でも異なっていてもよく、互いに連結して飽和もしくは不飽和の環を形成してもよい。
Ｒ^ａ、Ｒ^ｂは、それぞれ独立に、置換もしくは無置換の核炭素数５〜５０のアリール基又は置換もしくは無置換の核炭素数５〜５０の複素環基である。

（式（２）中、Ａｒ^１１及びＡｒ^１２は、それぞれ独立に、置換もしくは無置換の核炭素数６〜５０のアリール基、又は核原子数５〜５０の複素環基であり、
Ｒ^１〜Ｒ^８のいずれか１つが、置換もしくは無置換の核炭素数６〜５０のアリール基、又は置換もしくは無置換の核原子数５〜５０の複素環基であり、
置換もしくは無置換の核炭素数６〜５０のアリール基、又は置換もしくは無置換の核原子数５〜５０の複素環基であるＲ^１〜Ｒ^８以外のＲ^１〜Ｒ^８は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核炭素数６〜５０のアリールオキシ基、置換もしくは無置換の核炭素数６〜５０のアリールチオ基、置換もしくは無置換の炭素数２〜５０のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシル基から選ばれる基である。）
２．前記式（２）中のＲ^１、Ｒ^２、Ｒ^７及びＲ^８のいずれか１つが置換もしくは無置換の核炭素数６〜５０のアリール基又は置換もしくは無置換の核原子数５〜５０の複素環基である１に記載の有機発光媒体。
３．前記式（２）中のＲ^１及びＲ^８の一方が置換もしくは無置換の核炭素数６〜５０のアリール基又は置換もしくは無置換の核原子数５〜５０の複素環基であり、他方が水素原子である２に記載の有機発光媒体。
４．前記式（２）中のＲ^１、Ｒ^２、Ｒ^７及びＲ^８のいずれか１つが置換もしくは無置換の核炭素数６〜５０のアリール基である２に記載の有機発光媒体。
５．前記式（２）中のＲ^１及びＲ^８の一方が置換もしくは４に記載の有機発光媒体。
６．前記置換もしくは無置換の核炭素数６〜５０のアリール基が、置換もしくは無置換のフェニル基、ナフチル基、フルオレニル基又はフェナントリル基である５に記載の有機発光媒体。
７．前記式（２）におけるＡｒ^１１が、置換もしくは無置換の核原子数５〜５０の複素環基である１〜６のいずれかに記載の有機発光媒体。
８．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ独立に、置換もしくは無置換の核炭素数１０〜５０の縮合アリール基である１〜６のいずれかに記載の有機発光媒体。
９．前記式（２）におけるＡｒ^１１及びＡｒ^１２が同一の基である８に記載の有機発光媒体。
１０．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の９−フェナントレニル基である９に記載の有機発光媒体。
１１．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の２−ナフチル基である９に記載の有機発光媒体。
１２．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の１−ナフチル基である９に記載の有機発光媒体。
１３．前記式（２）におけるＡｒ^１１及びＡｒ^１２が異なる基である８に記載の有機発光媒体。
１４．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ置換もしくは無置換のフェニル基である１〜９及び１３のいずれかに記載の有機発光媒体。
１５．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ置換もしくは無置換の各炭素数６〜３０のアリール基又は置換もしくは無置換の核原子数５〜３０の複素環基が置換されたフェニル基である１４に記載の有機発光媒体。
１６．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ置換もしくは無置換の９−フェナントレニル基、置換もしくは無置換の１−ナフチル基、置換もしくは無置換の２−ナフチル基、置換もしくは無置換のフルオランテニル基、及び置換もしくは無置換のピレニル基のいずれかである１３に記載の有機発光媒体。
１７．前記式（２）におけるＡｒ^１１及びＡｒ^１２の一方が置換もしくは無置換のフェニル基であり、他方が置換もしくは無置換の核炭素数１０〜５０の縮合アリール基である１３に記載の有機発光媒体。
１８．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換の１−ナフチル基である１７に記載の有機発光媒体。
１９．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換の２−ナフチル基である１７に記載の有機発光媒体。
２０．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換のフルオランテニル基である１７に記載の有機発光媒体。
２１．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換のピレニル基である１７に記載の有機発光媒体。
２２．前記式（１）中のＲ^ａ、Ｒ^ｂが、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、又は置換若しくは無置換のフルオレニル基である１〜２１のいずれかに記載の有機発光媒体。
２３．前記式（１）中のＡｒ^１〜Ａｒ^４が、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換のフルオレニル基、又は置換若しくは無置換のジベンゾフラニル基から選ばれる基である１〜２２のいずれかに記載の有機発光媒体。
２４．前記式（１）中のＡｒ^１〜Ａｒ^４の少なくとも一つが、置換若しくは無置換のフルオレニル基である２３に記載の有機発光媒体。
２５．前記式（１）中のＲ^２１〜Ｒ^２４が、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のメチル基、置換若しくは無置換のエチル基、置換若しくは無置換のイソプロピル基、置換若しくは無置換のｔ−ブチル基、置換若しくは無置換のシクロプロピル基、置換若しくは無置換のシクロペンチル基、置換若しくは無置換のシクロヘキシル基、置換若しくは無置換のトリメチルシリル基、又はシアノ基である１〜２４のいずれかに記載の有機発光媒体。
２６．陽極と陰極と、
前記陽極と陰極の間にある１以上の有機薄膜層とを有し、
前記有機薄膜層の少なくとも一層が１〜２５のいずれかに記載の有機発光媒体を含有する有機エレクトロルミネッセンス素子。
２７．前記有機発光媒体を含有する有機薄膜層が発光層である２６に記載の有機エレクトロルミネッセンス素子。As a result of intensive studies to solve the above problems, the present inventors have found that the following problems can be solved by the present invention.
According to the present invention, the following organic light emitting media and the like are provided.
1, an organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (2).

(In formula (1), Ar ^{1 to} Ar ⁴ are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms. .
R ^{21 to} R ²⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms, or a substituted or unsubstituted nuclear carbon. An aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 50 carbon atoms An oxy group, a substituted or unsubstituted arylamino group having 5 to 50 nuclear carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms, A substituted or unsubstituted silyl group, a cyano group, or a halogen atom.
n1 to n4 are each independently an integer of 0 to 5, and when each of n1 to n4 is 2 or more, R ^{21 to} R ²⁴ may be the same or different, and are connected to each other to be saturated or An unsaturated ring may be formed.
R ^a and R ^b are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms.

(In the formula (2), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
Any one of R ^{1 to} R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or ^R 1 to R ⁸ other than ^R 1 to R ⁸ is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms each independently A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or An unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted carbon number It is a group selected from 2 to 50 alkoxycarbonyl groups, substituted or unsubstituted silyl groups, carboxy groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups. )
2. Any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted nuclear atom having 5 to 50 nuclear atoms. 2. The organic light-emitting medium according to 1, which is a heterocyclic group.
3. ^One of R ¹ and R ⁸ in the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and the other is 2. The organic light-emitting medium according to 2, which is a hydrogen atom.
4). 3. The organic light-emitting medium according to 2, wherein any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
5. 5. The organic luminescent medium according to 4, wherein ^one of R ¹ and R ^{8 in} the formula (2) is substituted or 4.
6). 6. The organic light-emitting medium according to 5, wherein the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms is a substituted or unsubstituted phenyl group, naphthyl group, fluorenyl group, or phenanthryl group.
7). The organic light-emitting medium according to any one of 1 to 6, wherein Ar ¹¹ in the formula (2) is a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
8). The organic light emitting medium according to any one of 1 to 6, wherein Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms.
9. 9. The organic light-emitting medium according to 8, wherein Ar ¹¹ and Ar ¹² in the formula (2) are the same group.
10. 10. The organic light emitting medium according to 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 9-phenanthrenyl groups.
11. 10. The organic light emitting medium according to 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 2-naphthyl groups.
12 10. The organic light emitting medium according to 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 1-naphthyl groups.
13. 9. The organic light-emitting medium according to 8, wherein Ar ¹¹ and Ar ¹² in the formula (2) are different groups.
14 The organic light-emitting medium according to any one of 1 to 9 and 13, wherein Ar ¹¹ and Ar ¹² in the formula (2) are each a substituted or unsubstituted phenyl group.
15. Ar ¹¹ and Ar ¹² in the formula (2) are each a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted phenyl group substituted with a heterocyclic group having 5 to 30 nuclear atoms. 15. The organic light-emitting medium according to 14, which is
16. Ar ¹¹ and Ar ¹² in the above formula (2) are each substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted 1-naphthyl group, substituted or unsubstituted 2-naphthyl group, substituted or unsubstituted full 14. The organic light-emitting medium according to 13, which is either an oranthenyl group and a substituted or unsubstituted pyrenyl group.
17. 14. The organic light-emitting medium according to 13, wherein one of Ar ¹¹ and Ar ¹² in the formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. .
18. 18. The organic light-emitting medium according to 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 1-naphthyl group.
19. 18. The organic light-emitting medium according to 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 2-naphthyl group.
20. 18. The organic light-emitting medium according to 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted fluoranthenyl group.
21. 18. The organic light-emitting medium according to 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted pyrenyl group.
22. Any one of 1 to 21 wherein R ^a and R ^b in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group; The organic luminescent medium described in 1.
23. Ar ^{1 to} Ar ⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuran. The organic light-emitting medium according to any one of 1 to 22, which is a group selected from a nyl group.
24. 24. The organic light-emitting medium according to 23, wherein at least one of Ar ^{1 to} Ar ⁴ in the formula (1) is a substituted or unsubstituted fluorenyl group.
25. R ^{21 to} R ²⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, A substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted trimethylsilyl group, or a cyano group 1 to 25. The organic light emitting medium according to any one of 24.
26. An anode and a cathode;
Having one or more organic thin film layers between the anode and the cathode;
The organic electroluminescent element in which at least one layer of the said organic thin film layer contains the organic luminescent medium in any one of 1-25.
27. 27. The organic electroluminescence device according to 26, wherein the organic thin film layer containing the organic light emitting medium is a light emitting layer.

  According to the present invention, it is possible to provide an organic EL element that can obtain high luminous efficiency and has a long lifetime, and an organic light emitting medium that can be used for an organic thin film layer of the organic EL element.

[Organic light-emitting medium]
The organic light-emitting medium of the present invention contains a specific diaminopyrene derivative and a specific anthracene derivative. The organic light-emitting medium contributes to light emission as a constituent component of the organic thin film layer of the organic EL element, and is present in the layer as, for example, a deposit. And when it uses for an organic EL element, high luminous efficiency can be acquired and it can contribute to lifetime extension. Hereinafter, the diaminopyrene derivative and the anthracene derivative according to the present invention will be described.

式（１）中、Ａｒ^１〜Ａｒ^４は、それぞれ独立に、置換もしくは無置換の核炭素数５〜５０のアリール基又は置換もしくは無置換の核炭素数５〜５０の複素環基である。
Ｒ^２１〜Ｒ^２４は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数５〜５０のアリール基、置換もしくは無置換の核炭素数６〜５０のアラルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数５〜５０のアリールオキシ基、置換もしくは無置換の核炭素数５〜５０のアリールアミノ基、置換もしくは無置換の炭素数１〜２０のアルキルアミノ基、置換もしくは無置換の核炭素数５〜５０の複素環基、置換もしくは無置換のシリル基、シアノ基又はハロゲン原子である。
ｎ１〜ｎ４は、それぞれ独立に、０〜５の整数であり、ｎ１〜ｎ４のそれぞれが２以上の場合、Ｒ^２１〜Ｒ^２４は、それぞれ同一でも異なっていてもよく、互いに連結して飽和もしくは不飽和の環を形成してもよい。
Ｒ^ａ、Ｒ^ｂは、それぞれ独立に、置換もしくは無置換の核炭素数５〜５０のアリール基又は置換もしくは無置換の核炭素数５〜５０の複素環基である。(Diaminopyrene derivative)
The diaminopyrene derivative according to the present invention is represented by the following formula (1).

In formula (1), Ar ^{1 to} Ar ⁴ are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms.
R ^{21 to} R ²⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms, or a substituted or unsubstituted nuclear carbon. An aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 50 carbon atoms An oxy group, a substituted or unsubstituted arylamino group having 5 to 50 nuclear carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms, A substituted or unsubstituted silyl group, a cyano group, or a halogen atom.
n1 to n4 are each independently an integer of 0 to 5, and when each of n1 to n4 is 2 or more, R ^{21 to} R ²⁴ may be the same or different, and are connected to each other to be saturated or An unsaturated ring may be formed.
R ^a and R ^b are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms.

Preferably, the diaminopyrene derivative is represented by the following formula (1 ′).

In formula (1 ′), R ²¹ ′ to R ²⁴ ′ each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. A substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 20 carbon atoms, and the same When there are one or two sets of adjacent alkyl groups on the benzene ring, the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
n1'-n4 'is an integer of 1-5 each independently.
R ^a ′ and R ^b ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.

In the present invention, the hydrogen atom includes a deuterium atom.
“Nuclear carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. The “nuclear atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). For example, a phenyl group substituted with a naphthyl group is a substituted aryl group having 16 carbon atoms, and a phenyl group substituted with a methyl group is an aryl group having 6 substituted nuclear carbon atoms.
In the definition of each formula of the present invention, the substituent in “substituted or unsubstituted...” Is an alkyl group, aryl group, cycloalkyl group, alkoxy group, heterocyclic group, aralkyl group as described later. , An aryloxy group, an arylthio group, an alkoxycarbonyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxy group, and the like. Preferred are an alkyl group, an aryl group, a cycloalkyl group, and a heterocyclic group.

In Formula (1), Ar ^{1 to} Ar ⁴ are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms. . n1-4 are each preferably 1-5, more preferably an integer of 1-3.
Specific examples of the substituted or unsubstituted aryl group represented by Ar ^{1 to} Ar ⁴ include a phenyl group, a naphthyl group, an anthryl group, a naphthacenyl group, a pyrenyl group, a fluoranthenyl group, a chrysenyl group, a fluorenyl group, a perylenyl group, Biphenyl group, terphenyl group, tolyl group, ethylphenyl group, p-t-butylphenyl group and the like can be mentioned, and phenyl group, naphthyl group and fluorenyl group are preferable.

Examples of the substituted or unsubstituted heterocyclic group represented by Ar ^{1 to} Ar ⁴ include imidazole, benzimidazole, pyrrole, furan, thiophene, benzothiophene, oxadiazoline, indoline, carbazole, pyridine, quinoline, isoquinoline, benzoquinone, and pyralazine. , Imidazolidine, piperidine, dibenzofuran, benzofuran, dibenzothiophene, and the like, preferably benzimidazole, thiophene, carbazole, and dibenzofuran.

In Formula (1), R ^{21 to} R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted carbon number of 1 to 50 (preferably having 1 to 20 carbon atoms, and particularly preferably having 1 to 4 carbon atoms). ), A substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms (preferably 5 to 20 carbon atoms, particularly preferably 6 to 10 carbon atoms), substituted or unsubstituted 6 carbon atoms -50 aralkyl group (preferably having 6 to 20 nuclear carbon atoms), substituted or unsubstituted cycloalkyl group having 3 to 50 (preferably 3 to 12 nuclear carbon atoms) cycloalkyl group, substituted or unsubstituted carbon An alkoxy group having 1 to 50 (preferably 1 to 6 carbons), a substituted or unsubstituted aryloxy group having 5 to 50 (preferably 5 to 18 carbon atoms) nuclear carbon, a substituted or unsubstituted Nuclear carbon number 5-50 ( Preferably, the arylamino group having 5 to 18 nuclear carbon atoms, the substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms (preferably 1 to 6 carbon atoms), the substituted or unsubstituted nuclear carbon number 5 A heterocyclic group of ˜50 (preferably having a carbon number of 5 to 20), a substituted or unsubstituted silyl group, a cyano group or a halogen atom.

Examples of the substituted or unsubstituted alkyl group represented by R ^{21 to} R ²⁴ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a heptyl group. Group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α , Α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group and the like.
From the viewpoint of stability, among the above, an alkyl group having 1 to 4 carbon atoms is preferable. For example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, or a tert-butyl group. is there.

Examples of the substituted or unsubstituted aryl group for R ^{21 to} R ²⁴ are the same as those for Ar ^{1 to} Ar ⁴ .

Examples of the substituted or unsubstituted aralkyl group of R ^{21 to} R ²⁴ include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, methylbenzyl group, cyanobenzyl group Etc.

Examples of the substituted or unsubstituted cycloalkyl group of R ^{21 to} R ²⁴ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a bicycloheptyl group, and a bicyclooctyl group. Group, tricycloheptyl group, adamantyl group, etc., and cyclopentyl group, cyclohexyl group, cycloheptyl group, bicycloheptyl group, bicyclooctyl group, adamantyl group, preferably cyclopropyl group, cyclobutyl group, cyclopentyl group, A cyclohexyl group and a cycloheptyl group.

Examples of the substituted or unsubstituted alkoxy group represented by R ^{21 to} R ²⁴ include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, and various pentyloxy groups. Group, various hexyloxy groups and the like.
Examples of the substituted or unsubstituted aryloxy group for R ^{21 to} R ²⁴ include a phenoxy group, a tolyloxy group, and a naphthyloxy group.

Examples of the substituted or unsubstituted arylamino group of R ^{21 to} R ²⁴ include a diphenylamino group, a ditolylamino group, a dinaphthylamino group, and a naphthylphenylamino group.
Examples of the substituted or unsubstituted alkylamino group for R ^{21 to} R ²⁴ include a dimethylamino group, a diethylamino group, and a dihexylamino group.
Examples of the substituted or unsubstituted heterocyclic group for R ^{21 to} R ²⁴ are the same as those for Ar ^{1 to} Ar ⁴ .

Examples of the substituent for the silyl group of R ^{21 to} R ²⁴ include an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms. Examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and pentyl groups. And an alkyl group having 1 to 5 carbon atoms is preferred. Examples of the aryl group having 6 to 14 carbon atoms include a phenyl group, a naphthyl group, and an anthryl group, and an aryl group having 6 to 10 carbon atoms is preferable. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, and an alkoxy group having 1 to 5 carbon atoms is preferable.
Examples of the halogen atom of R ²¹ to R ^24, for example, a fluorine atom, a chlorine atom, and bromine atom.

In Formula (1), n1-n4 represents the integer of 0-5 each independently, and it is still more preferable in it being 0-3.
When each of n1 to n4 is 2 or more, R ^{21 to} R ²⁴ may be the same as or different from each other, and may be connected to each other to form a saturated or unsaturated ring.
Examples of the ring include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane and cyclohexane, cycloalkanes having 4 to 12 carbon atoms such as cyclobutene, cyclopentene, cyclohexene, cycloheptene and cyclooctene, cyclohexadiene and cyclohepta. Examples thereof include cycloalkadiene having 6 to 12 carbon atoms such as diene and cyclooctadiene.

The substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms and the substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms for R ^a and R ^b are the same as those for Ar ^{1 to} Ar ⁴ .

  A substituted or unsubstituted aryl group of formula (1 ′), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted silyl group, an adjacent alkyl The substituted or unsubstituted divalent linking group formed by the group is the same as described above.

In a preferred embodiment of the present invention, the diaminopyrene derivative of the formula (1) is represented by the following formula.

In the above formula, R ^{21 to} R ²⁴ , R ^a and R ^b are the same as described above. R ^{21 to} R ²⁴ may be the same or different from each other, but it is preferable that R ²¹ and R ²³ , and R ²² and R ²⁴ are the same. R ^a and R ^b may be the same or different, but are preferably the same.

Specific examples of the diaminopyrene derivative represented by the formula (1) include compounds represented by the following formula.

（式（２）中、Ａｒ^１１及びＡｒ^１２は、それぞれ独立に、置換もしくは無置換の核炭素数６〜５０のアリール基、又は核原子数５〜５０の複素環基であり、
Ｒ^１〜Ｒ^８のいずれか１つが、置換もしくは無置換の核炭素数６〜５０のアリール基、又は置換もしくは無置換の核原子数５〜５０の複素環基であり、
置換もしくは無置換の核炭素数６〜５０のアリール基、又は置換もしくは無置換の核原子数５〜５０の複素環基であるＲ^１〜Ｒ^８以外のＲ^１〜Ｒ^８は、それぞれ独立に、水素原子、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核炭素数６〜５０のアリールオキシ基、置換もしくは無置換の核炭素数６〜５０のアリールチオ基、置換もしくは無置換の炭素数２〜５０のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシル基から選ばれる基である。）置換基の具体例としては前述した通りである。(Anthracene derivative)
The anthracene derivative according to the present invention is represented by the following formula (2).

(In the formula (2), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
Any one of R ^{1 to} R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or ^R 1 to R ⁸ other than ^R 1 to R ⁸ is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms each independently A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or An unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted carbon number It is a group selected from 2 to 50 alkoxycarbonyl groups, substituted or unsubstituted silyl groups, carboxy groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups. ) Specific examples of the substituent are as described above.

The anthracene derivative of the present invention is preferably a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted nuclear atom number of 5 or any ^one of R ¹ , R ² , R ⁷ and R ^8. 50, more preferably one of R ¹ and R ⁷ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. Yes, the other is a hydrogen atom, or one of R ² and R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms The other is a hydrogen atom.

In the anthracene derivative of the present invention, preferably any one of R ¹ , R ² , R ⁷ and R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, more preferably R ¹ and R ^7. Is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, the other is a hydrogen atom, or one of R ² and R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. And the other is a hydrogen atom.
The substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms is preferably a substituted or unsubstituted phenyl group, naphthyl group or phenanthryl group.

In addition to the requirements regarding R ^{1 to} R ^{8, the} anthracene derivative according to the present invention is preferably any of the following anthracene derivatives (A), (B), and (C), It is selected according to the configuration and desired characteristics.

(Anthracene derivative (A))
In the anthracene derivative, Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. The anthracene derivative can be classified into a case where Ar ¹¹ and Ar ¹² are the same substituted or unsubstituted condensed aryl group and a case where they are different substituted or unsubstituted condensed aryl groups.
Specifically, anthracene derivatives represented by the following formulas (2-1) to (2-3) (preferably Ar ¹¹ and Ar ¹² are the same), and Ar ¹¹ and Ar ¹² in the formula (2) are Anthracene derivatives which are different substituted or unsubstituted fused aryl groups are exemplified.

（式（２−１）中、Ｒ^１〜Ｒ^８は前記と同様であり、
Ｒ^１１は水素原子、置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核原子数５〜５０の複素環基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核炭素数６〜５０のアリールオキシ基、置換もしくは無置換の核炭素数６〜５０のアリールチオ基、置換もしくは無置換の炭素数２〜５０のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシル基から選ばれる基であり、
ａは０〜９の整数である。ａが２以上の整数の場合、複数あるＲ^１１は、２つの置換もしくは無置換のフェナントレニル基が同一であることを条件に、それぞれが同一でも異なっていてもよい。）In the anthracene derivative represented by the following formula (2-1), Ar ¹¹ and Ar ¹² are substituted or unsubstituted 9-phenanthrenyl groups.

(In formula (2-1), R ^{1 to} R ⁸ are the same as above,
R ¹¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxy A group selected from a group, a halogen atom, a cyano group, a nitro group and a hydroxyl group,
a is an integer of 0-9. When a is an integer of 2 or more, a plurality of R ^{11 s} may be the same or different on condition that two substituted or unsubstituted phenanthrenyl groups are the same. )

（式（２−２）中、Ｒ^１〜Ｒ^８及びＲ^１１は前記と同様であり、
ｂは１〜７の整数である。ｂが２以上の整数の場合、複数あるＲ^１１は、それぞれが同一でも異なっていてもよい。）In the anthracene derivative represented by the following formula (2-2), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 2-naphthyl groups.

(In formula (2-2), R ^{1 to} R ⁸ and R ¹¹ are the same as above,
b is an integer of 1-7. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different. )

（式（２−２）中、Ｒ^１〜Ｒ^８、Ｒ^１１及びｂは前記と同様である。また、ｂが２以上の整数の場合、それぞれが同一でも異なっていてもよい。）In the anthracene derivative represented by the following formula (2-3), Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 1-naphthyl groups.

(In formula (2-2), R ^{1 to} R ⁸ , R ¹¹ and b are the same as described above. When b is an integer of 2 or more, they may be the same or different.)

In addition to the anthracene derivatives represented by the above formulas (2-1) to (2-3), an anthracene derivative in which Ar ¹¹ and Ar ¹² in the formula (2) are the same substituted or unsubstituted fluoranthenyl group, Anthracene derivatives in which Ar ¹¹ and Ar ¹² in Formula (2) are the same substituted or unsubstituted pyrenyl group are also preferred.

As an anthracene derivative in which Ar ¹¹ and Ar ¹² in Formula (2) are different substituted or unsubstituted condensed aryl groups, Ar ¹¹ and Ar ¹² are represented by Formulas (2-1) to (2-3), substituted or unsubstituted It is preferably any of a substituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, and a substituted or unsubstituted fluoranthenyl group.
Specifically, when Ar ¹¹ is a 1-naphthyl group and Ar ¹² is a 2-naphthyl group, when Ar ¹¹ is a 1-naphthyl group and Ar ¹² is a 9-phenanthryl group, and when Ar ¹¹ is 2- This is a case where the naphthyl group and Ar ¹² are 9-phenanthryl groups.

(Anthracene derivative (B))
In the anthracene derivative, one of Ar ¹¹ and Ar ¹² in Formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) and (2-5).

（式（２−４）中、Ｒ^１〜Ｒ^８、Ｒ^１１及びｂは前記と同様であり、
Ａｒ^６は置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核原子数５〜５０の複素環基、９，９−ジメチルフルオレン−１−イル基、９，９−ジメチルフルオレン−２−イル基、９，９−ジメチルフルオレン−３−イル基、９，９−ジメチルフルオレン−４−イル基、ジベンゾフラン−１−イル基、ジベンゾフラン−２−イル基、ジベンゾフラン−３−イル基、又はジベンゾフラン−４−イル基である。また、Ａｒ^６はそれが結合しているベンゼン環と共に、置換もしくは無置換のフルオレニル基又は置換もしくは無置換のジベンゾフルオレニル基を形成していてもよい。ｂが２以上の整数の場合、複数あるＲ^１１は、それぞれが同一でも異なっていてもよい。）In the anthracene derivative represented by the following formula (2-4), Ar ¹¹ in the formula (2) is a substituted or unsubstituted 1-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In Formula (2-4), R ^{1 to} R ⁸ , R ¹¹ and b are the same as above,
Ar ⁶ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Or an unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a 9,9-dimethylfluoren-1-yl group, and a 9,9-dimethylfluorene-2- Yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3-yl group, or dibenzofuran It is a -4-yl group. Ar ⁶ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁶ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different. )

（式（２−５）中、Ｒ^１〜Ｒ^８、Ｒ^１１及びｂは前記と同様であり、
Ａｒ^７は、置換もしくは無置換の核炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の核原子数５〜５０の複素環基、ジベンゾフラン−１−イル基、ジベンゾフラン−２−イル基、ジベンゾフラン−３−イル基、又はジベンゾフラン−４−イル基である。また、Ａｒ^７はそれが結合しているベンゼン環と共に、置換もしくは無置換のフルオレニル基又は置換もしくは無置換のジベンゾフルオレニル基を形成していてもよい。ｂが２以上の整数の場合、複数あるＲ^１１は、それぞれが同一でも異なっていてもよい。）In the anthracene derivative represented by the following formula (2-5), Ar ¹¹ in the formula (2) is a substituted or unsubstituted 2-naphthyl group, and Ar ¹² is a substituted or unsubstituted phenyl group. .

(In formula (2-5), R ^{1 to} R ⁸ , R ¹¹ and b are the same as above,
Ar ⁷ is a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted group Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a dibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-yl group, or a dibenzofuran-4-yl group. Ar ⁷ may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar ⁷ is bonded. When b is an integer of 2 or more, the plurality of R ¹¹ may be the same or different. )

In addition to the anthracene derivatives represented by the above formulas (2-4) and (2-5), Ar ¹¹ in formula (2) is a substituted or unsubstituted fluoranthenyl group, and Ar ¹² is substituted. Alternatively, an anthracene derivative which is an unsubstituted phenyl group is also preferable.

（式（２−６）中、Ｒ^１〜Ｒ^８及びＡｒ^６は前記と同様であり、
Ａｒ^５は置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核炭素数１〜５０のアルキル基、置換もしくは無置換の核炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数７〜５０のアラルキル基、又は置換もしくは無置換の核原子数５〜５０の複素環基であり、Ａｒ^５とＡｒ^６はそれぞれ独立に選択される。）

（式（２−６−１）中、Ｒ^１〜Ｒ^８は前記と同様である。）

（式（２−６−２）中、Ｒ^１〜Ｒ^８は前記と同様である。Ａｒ^８は置換もしくは無置換の核炭素数１０〜２０の縮合アリール基である。）

（式（２−６−３）中、Ｒ^１〜Ｒ^８は式（２）と同様である。
Ａｒ^５ａ及びＡｒ^６ａはそれぞれ独立に、置換もしくは無置換の核炭素数１０〜２０の縮合アリール基である。）(Anthracene derivative (C))
The anthracene derivative is represented by the following formula (2-6), specifically, any one of the following formulas (2-6-1), (2-6-2), and (2-6-3) It is preferable that it is a derivative represented.

(In formula (2-6), R ^{1 to} R ⁸ and Ar ⁶ are the same as above,
Ar ⁵ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Alternatively, it is an unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, and Ar ⁵ and Ar ⁶ are each independently selected. )

(In formula (2-6-1), R ^{1 to} R ⁸ are the same as described above.)

(In formula (2-6-2), R ^{1 to} R ⁸ are the same as described above. Ar ⁸ is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.)

(In formula (2-6-3), R ^{1 to} R ⁸ are the same as in formula (2).
Ar ^5a and Ar ^6a are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms. )

The aryl group having 6 to 50 nuclear carbon atoms of R ^{1 to} R ⁸ , R ¹¹ , Ar ⁵ and Ar ⁶ , Ar ¹¹ and Ar ¹² includes a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a 1-anthryl group. 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 6-chrysenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4- Benzo [c] phenanthryl group, 5-benzo [c] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chryseni Group, 2-benzo [g] chrysenyl group, 3-benzo [g] chrysenyl group, 4-benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl group, 7-benzo [G] Chrysenyl group, 8-benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group , 13-benzo [g] chrysenyl group, 14-benzo [g] chrysenyl group, 1-triphenyl group, 2-triphenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group 9-fluorenyl group, 9,9-dimethylfluoren-2-yl group, benzofluorenyl group, dibenzofluorenyl group, 2-biphenylyl group, 3-biphenyl Yl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m -Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) Phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl- 4-yl group, etc. Preferably, an unsubstituted phenyl group, a substituted phenyl group, and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms (for example, 1-naphthyl group, 2-naphthyl group, 9 -Phenanthryl group), substitution Properly unsubstituted fluorenyl group (2-fluorenyl group), and substituted or unsubstituted pyrenyl group (1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group). As the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, the above-described groups are preferable.

Further, Ar ^5a , Ar ^6a and Ar ⁸ having a condensed aryl group having 10 to 20 nuclear carbon atoms include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1 -Phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4 -A pyrenyl group, 2-fluorenyl group, etc. are mentioned. In particular, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group) and fluorenyl group (2-fluorenyl group) are preferable. As the substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms, the above-described groups are preferable.

Examples of the heterocyclic group having 5 to 50 nuclear atoms of R ^{1 to} R ⁸ , Ar ¹¹ , Ar ¹² , R ¹¹ and Ar ^{5 to} Ar ⁷ include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl Group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group Group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl Group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-iso Nzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, quinolyl Group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group Group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1- Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthroline-3-yl group, 1,7-phenanthroline -4-yl group, 1,7-phenanthroline-5-yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline- 4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1 , 8-phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5 -Yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenane Lorin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group 2,9-phenanthroline-1-yl group, 2,9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline -6-yl group, 2,9-phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline 6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-yl group, 2 , 7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline-8 -Yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3- Phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) ) Pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indole group Group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, and 4-t-butyl-3-indolyl group and the like. Preferably, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group Group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group. As the substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, the above-described groups are preferable.

Examples of the alkyl group having 1 to 50 carbon atoms of R ^{1 to} R ⁸ , R ¹¹ and Ar ^{5 to} Ar ⁷ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and isobutyl group. , T-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1, 2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3- Lichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3 -Diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1 , 3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, Nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2, A 3-trinitropropyl group and the like can be mentioned. Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group and t-butyl group. As a substituted or unsubstituted C1-C50 alkyl group, the above-mentioned group is preferable.

Examples of the cycloalkyl group having 3 to 50 nuclear carbon atoms of R ^{1 to} R ⁸ , R ¹¹ and Ar ^{5 to} Ar ⁷ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 1-adamantyl group. Group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like. Preferably, they are a cyclopentyl group and a cyclohexyl group. As the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, the above-described groups are preferable.

The alkoxy group having 1 to 50 carbon atoms of R ^{1 to} R ⁸ and R ¹¹ is a group represented by —OZ, and Z is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R ^{1 to} R ^8. Selected from the group.

R ^{1 to} R ⁸ , R ^11, and Ar ^{5 to} Ar ⁷ having ⁷ to 50 carbon atoms (the aryl moiety has 6 to 49 carbon atoms and the alkyl moiety has 1 to 44 carbon atoms) include a benzyl group and 1-phenyl Ethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β- Naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p -Chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodo Benzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group O-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like. As a substituted or unsubstituted C7-50 aralkyl group, the above-mentioned group is preferable.

The aryloxy group and arylthio group having 6 to 50 nuclear carbon atoms of R ^{1 to} R ⁸ and R ¹¹ are represented as —OY and —SY, respectively, and Y is a substituted or unsubstituted nucleus of R ^{1 to} R ^8. It is selected from aryl groups having 6 to 50 carbon atoms.

R ¹ to R ⁸ and number 2-50 alkoxycarbonyl group having a carbon of ^{R 11} (alkyl moiety from 1 to 49 carbon atoms) is represented as -COOZ, Z is a substituted or unsubstituted carbon atoms of the ^R 1 to R ⁸ It is selected from the alkyl groups having 1 to 49.

Examples of the substituted silyl group of R ^{1 to} R ⁸ and R ¹¹ include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.
These substituents may further have a substituent, and are preferably an aryl group, a heterocyclic group, an alkyl group, a cycloalkyl group, and a silyl group.
These preferred specific examples are as described above.
The expression “substituted or unsubstituted” described above further has a substituent such as an alkyl group, a cycloalkyl group, an alkoxy group, a cyano group, a silyl group, an aryl group, a heterocyclic group, and a halogen atom. Preferably an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and more preferably an aryl group or a heterocyclic group. Specific examples of these substituents are as described above.

Examples of the halogen atom for R ^{1 to} R ⁸ and R ¹¹ include fluorine, chlorine, bromine and iodine.

The anthracene derivative of the present invention is preferably an anthracene derivative in which the substituent consists only of an aryl group and / or a heterocyclic group, and most preferably an anthracene derivative in which the substituent consists only of an aryl group.
The hydrogen atom bonded to the anthracene derivative of the present invention may be a deuterium atom.

Specific examples of the anthracene derivative represented by the formula (2) of the present invention include the following.

  The diaminopyrene derivative represented by the formula (1) is, for example, introduced into a dibromopyrene obtained by bromination of commercially available pyrene by a known method, then brominated again, and corresponding to the reaction under a metal catalyst. It can be synthesized by reacting with a secondary amine compound. Moreover, the anthracene derivative represented by Formula (2) is compoundable by the method of WO2004 / 018587, for example.

The organic light-emitting medium of the present invention is in a state where an anthracene derivative represented by the diaminopyrene derivative formula (2) represented by the formula (1) as described above coexists.
The mass ratio of the diaminopyrene derivative represented by the formula (1) and the anthracene derivative represented by the formula (2) is preferably 50:50 to 0.1: 99.9, and 20:80 to 1 : 99 is more preferable.

[Organic EL device]
The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between an anode and a cathode. When the organic thin film layer is a plurality of layers, one layer is a light emitting layer. When the organic thin film layer is a single layer, a light emitting layer as an organic thin film layer is formed between the anode and the cathode. At least one of the organic thin film layers (preferably the light emitting layer) contains the organic light emitting medium of the present invention, and further transports holes injected from the anode or electrons injected from the cathode to the light emitting material. Further, a hole injection material or an electron injection material may be contained. The organic light emitting medium of the present invention has high light emission characteristics.

  Further, the organic EL device of the present invention is an organic EL device in which an organic thin film layer comprising at least two layers including at least a light emitting layer is sandwiched between a cathode and an anode, and the organic EL device of the present invention is interposed between the anode and the light emitting layer. It is also preferable to have an organic layer whose main component is a luminescent medium. Examples of the organic layer include a hole injection layer and a hole transport layer.

In the present invention, organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
In addition to the organic light-emitting medium of the present invention, further known light-emitting materials, doping materials, hole-injecting materials, and electron-injecting materials can be used for the plurality of layers as necessary. The organic EL element can prevent the brightness | luminance and lifetime fall by quenching by making the said organic thin film layer into a multilayer structure. If necessary, a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer for injecting electrons from an electrode is called an electron injection layer, and a layer for receiving electrons from the electron injection layer and transporting electrons to a light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.

  Examples of the host material or doping material that can be used in the light emitting layer together with the organic light emitting medium of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentane. Fused aromatic compounds such as pentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like Derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinate) aluminum, triarylamine derivatives, styrylamine Conductors, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives, quinacridone derivatives, etc. However, it is not limited to these.

  As a hole injection material, it has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or organic light emitting medium, and excitons generated in the light emitting layer The compound which prevents the movement to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl Examples include alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinyl carbazole, polysilane, and conductive polymer. However, it is not limited to these.

Among the hole injection materials that can be used in the organic EL device of the present invention, more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
Examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4. '-Diamine, N, N, N', N '-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N', N '-(4-methylphenyl) ) -1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-( Methylphenyl) -N, N ′-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, etc. Or oligomers having these aromatic tertiary amine skeletons Or is a polymer, but is not limited thereto.

Examples of the phthalocyanine (Pc) derivative include H ₂ Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl ₂ SiPc, (HO) AlPc, (HO) GaPc, Although there exist phthalocyanine derivatives and naphthalocyanine derivatives, such as VOPc, TiOPc, MoOPc, and GaPc-O-GaPc, it is not limited to these.

  Further, the organic EL device of the present invention includes a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or the hole injection layer, between the light emitting layer and the anode. Preferably formed.

As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer The compound which prevents the movement to and is excellent in thin film forming ability is preferable.
As specific examples of the electron injection material, 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable. As a specific example of the metal complex of the above 8-hydroxyquinoline or a derivative thereof, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinolato) aluminum is injected. It can be used as a material.

On the other hand, examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.

(In the above formula, Ar ¹ , Ar ² , Ar ³ , Ar ⁵ , Ar ⁶ , and Ar ⁹ each represent a substituted or unsubstituted aryl group, and may be the same or different from each other.
Ar ⁴ , Ar ⁷ and Ar ⁸ represent a substituted or unsubstituted arylene group, and may be the same or different.

Furthermore, what is represented by the following general formula (A)-(F) can also be used as an electron injection material.

(In General Formulas (A) and (B), A ^{1 to} A ³ are each independently a nitrogen atom or a carbon atom.
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms,
Ar ² is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or a divalent group thereof.
However, ^one of Ar ¹ and Ar ² is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms or a substituted or unsubstituted monoheterocondensed ring group having 5 to 60 nuclear atoms.
L ¹ , L ² and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or a substituted or unsubstituted An unsubstituted fluorenylene group.
R is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is 2 or more, a plurality of Rs may be the same or different and adjacent to each other. A plurality of R groups may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
R ¹ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. group, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or ^-L 1 ^-Ar 1 ^{-Ar 2.} The nitrogen-containing heterocyclic derivative represented by this.

HAr-L-Ar ¹ -Ar ² (C)
(Wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent,
L has a single bond, an arylene group having 6 to 60 nuclear carbon atoms which may have a substituent, a heteroarylene group having 5 to 60 nuclear atoms which may have a substituent, or a substituent. A fluorenylene group which may be
Ar ¹ is a divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms which may have a substituent,
Ar ² is an aryl group having 6 to 60 nuclear carbon atoms which may have a substituent or a heterocyclic group having 5 to 60 nuclear atoms which may have a substituent. The nitrogen-containing heterocyclic derivative represented by this.

(Wherein X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, alkoxy group, alkenyloxy group, alkynyloxy group, hydroxy group, substituted or unsubstituted aryl group, substituted Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring,
R _{1 to} R ₄ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, Alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, sulfanyl group, Silyl, carbamoyl, aryl, heterocyclic, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothi If the cyanate were group or cyano group, or adjacent a structure substituted or the unsubstituted rings are fused. A silacyclopentadiene derivative represented by:

Wherein R _{1 to} R ₈ and Z ₂ are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, or an alkoxy group. Or an aryloxy group,
X, Y and Z ₁ each independently represent a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group;
The substituents of Z ₁ and Z ₂ may be bonded to each other to form a condensed ring. N represents an integer of 1 to 3, and when n is 2 or more, Z ₁ may be different.
However, the case where n is 1, X, Y and R ₂ are methyl groups and R ₈ is a hydrogen atom or a substituted boryl group and the case where n is 3 and Z ₁ is a methyl group are not included. A borane derivative represented by:

［式中、環Ａ^１及びＡ^２は、置換基を有してよい互いに縮合した６員アリール環構造である。］[Wherein, Q ¹ and Q ² each independently represent a ligand represented by the following general formula (G),
L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, —OR ¹ (R ¹ is a hydrogen atom, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group) or —O—Ga-Q ³ (Q ⁴ ). (Q ³ and Q ⁴ are the same as Q ¹ and Q ² ). ]

[Wherein, rings A ¹ and A ² are 6-membered aryl ring structures condensed with each other which may have a substituent. ]

  This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.

The alkyl group, aryl group, heterocyclic group and the like described in the above-described hole injecting material, hole transporting material, and electron injecting material in the present invention are represented by R ²¹ to R ²⁴ in the chemical formula (1) or the chemical formula ( The examples described above for R ¹ to R ⁸ in 2) can be applied.

  A preferred form of the organic EL device of the present invention is a device containing a reducing dopant in the region for transporting electrons or the interface region between the cathode and the organic layer. Here, the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. Oxides, alkaline earth metal halides, rare earth metal oxides or rare earth metal halides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal organic complexes, alkaline earth metal organic complexes In addition, at least one substance selected from the group consisting of organic complexes of rare earth metals can be preferably used.

  More specifically, preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV). Particularly preferred are those having a work function of 2.9 eV or less, including at least one alkaline earth metal selected from the group consisting of: Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. . These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element. Further, as a reducing dopant having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable. Particularly, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.

In the present invention, an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, K ₂ O, Na ₂ S, Na ₂ Se, and Na ₂ O, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.

  In addition, as a semiconductor constituting the electron injection layer, an oxide containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. , Nitrides or oxynitrides, or a combination of two or more. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.

Next, as a cathode, what uses a metal, an alloy, an electroconductive compound, and a mixture thereof with a small work function (4 eV or less) as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li ₂ O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.

  Here, when light emitted from the light-emitting layer is extracted from the cathode, the transmittance of the cathode for light emission is preferably greater than 10%. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 nm.

  In general, since an organic EL element applies an electric field to an ultrathin film, pixel defects due to leaks and shorts are likely to occur. In order to prevent this, an insulating thin film layer may be inserted between the pair of electrodes.

  Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.

  In order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., it is possible to provide a protective layer on the surface of the device, or to protect the entire device with silicon oil, resin, etc. It is.

  As the conductive material used for the anode of the organic EL device of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.

In the organic EL device of the present invention, in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone. , Polysulfone, polyethersulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, Examples include polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, and polypropylene. It is.

  For the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.

  In the case of the wet film forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like to form a thin film, and any solvent may be used. In any organic thin film layer, an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film. Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

  The organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like. The material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.

（式中、Ｒ_１〜Ｒ_７は、それぞれ水素原子、炭素数１〜２０のアルキル基、炭素数３〜２０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換のシリル基、ハロゲン原子、又はシアノ基である。
Ｒ_１１〜Ｒ_１５及びＲ_２１〜Ｒ_２５は、それぞれ水素原子、炭素数１〜２０のアルキル基、炭素数３〜２０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の核炭素数６〜５０のアリール基、置換もしくは無置換の核炭素数１０〜５０の縮合芳香族基、置換もしくは無置換の核原子数５〜５０の複素環基、置換もしくは無置換のシリル基、ハロゲン原子、又はシアノ基である。
但し、Ｒ_１１〜Ｒ_１５及びＲ_２１〜Ｒ_２５の少なくとも１つが、置換もしくは無置換の核炭素数１０〜５０の縮合芳香族基、又は置換もしくは無置換の核原子数５〜５０の複素環基である。
Ａｒ_１は、置換もしくは無置換の核炭素数６〜５０のアリール基、又は置換もしくは無置換の核原子数５〜５０の複素環基である。
但し、Ａｒ_１はオルトフェニレン構造を含まない。）
２’．前記式（２）中のＲ^１、Ｒ^２、Ｒ^７及びＲ^８のいずれか１つが置換もしくは無置換の核炭素数６〜５０のアリール基又は置換もしくは無置換の核原子数５〜５０の複素環基である１’に記載の有機発光媒体。
３’．前記式（２）中のＲ^１及びＲ^８の一方が置換もしくは無置換の核炭素数６〜５０のアリール基又は置換もしくは無置換の核原子数５〜５０の複素環基であり、他方が水素原子である２’に記載の有機発光媒体。
４’．前記式（２）中のＲ^１、Ｒ^２、Ｒ^７及びＲ^８のいずれか１つが置換もしくは無置換の核炭素数６〜５０のアリール基である２’に記載の有機発光媒体。
５’．前記式（２）中のＲ^１及びＲ^８の一方が置換もしくは４’に記載の有機発光媒体。
６’．前記置換もしくは無置換の核炭素数６〜５０のアリール基が、置換もしくは無置換のフェニル基、ナフチル基、フルオレニル基又はフェナントリル基である５’に記載の有機発光媒体。
７’．前記式（２）におけるＡｒ^１１が、置換もしくは無置換の核原子数５〜５０の複素環基である１’〜６’のいずれかに記載の有機発光媒体。
８’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ独立に、置換もしくは無置換の核炭素数１０〜５０の縮合アリール基である１’〜６’のいずれかに記載の有機発光媒体。
９’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が同一の基である８’に記載の有機発光媒体。
１０’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の９−フェナントレニル基である９’に記載の有機発光媒体。
１１’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の２−ナフチル基である９’に記載の有機発光媒体。
１２’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、置換もしくは無置換の１−ナフチル基である９’に記載の有機発光媒体。
１３’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が異なる基である８’に記載の有機発光媒体。
１４’．前記式（２）におけるＡｒ_１１及びＡｒ_１２が、それぞれ置換もしくは無置換のフェニル基である１’〜９’及び１３’のいずれかに記載の有機発光媒体。
１５’．前記式（２）におけるＡｒ_１１及びＡｒ_１２が、それぞれ置換もしくは無置換の各炭素数６〜３０のアリール基又は置換もしくは無置換の核原子数５〜３０の複素環基が置換されたフェニル基である１４’に記載の有機発光媒体。
１６’．前記式（２）におけるＡｒ^１１及びＡｒ^１２が、それぞれ置換もしくは無置換の９−フェナントレニル基、置換もしくは無置換の１−ナフチル基、置換もしくは無置換の２−ナフチル基、置換もしくは無置換のフルオランテニル基、及び置換もしくは無置換のピレニル基のいずれかである１３’に記載の有機発光媒体。
１７’．前記式（２）におけるＡｒ^１１及びＡｒ^１２の一方が置換もしくは無置換のフェニル基であり、他方が置換もしくは無置換の核炭素数１０〜５０の縮合アリール基である１３’に記載の有機発光媒体。
１８’．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換の１−ナフチル基である１７’に記載の有機発光媒体。
１９’．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換の２−ナフチル基である１７’に記載の有機発光媒体。
２０’．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換のフルオランテニル基である１７’に記載の有機発光媒体。
２１’．前記置換もしくは無置換の核炭素数１０〜５０の縮合アリール基が、置換もしくは無置換のピレニル基である１７’に記載の有機発光媒体。
２２’．上記式（１）で表されるジアミノピレン誘導体と、上記式（２’）で表されるアントラセン誘導体とを含む有機発光媒体。
２３’．前記式（１）中のＲ^ａ、Ｒ^ｂが、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、又は置換若しくは無置換のフルオレニル基である１’〜２２’のいずれかに記載の有機発光媒体。
２４’．前記式（１）中のＡｒ^１〜Ａｒ^４が、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換のフルオレニル基、又は置換若しくは無置換のジベンゾフラニル基から選ばれる基である１’〜２３’のいずれかに記載の有機発光媒体。
２５’．前記式（１）中のＡｒ^１〜Ａｒ^４の少なくとも一つが、置換若しくは無置換のフルオレニル基である２４’に記載の有機発光媒体。
２６’．前記式（１）中のＲ^２１〜Ｒ^２４が、それぞれ独立に、置換若しくは無置換のフェニル基、置換若しくは無置換のメチル基、置換若しくは無置換のエチル基、置換若しくは無置換のイソプロピル基、置換若しくは無置換のｔ−ブチル基、置換若しくは無置換のシクロプロピル基、置換若しくは無置換のシクロペンチル基、置換若しくは無置換のシクロヘキシル基、置換若しくは無置換のトリメチルシリル基、又はシアノ基である１’〜２５’のいずれかに記載の有機発光媒体。
２７’．陽極と陰極と、
前記陽極と陰極の間にある１以上の有機薄膜層とを有し、
前記有機薄膜層の少なくとも一層が１’〜２６’のいずれかに記載の有機発光媒体を含有する有機エレクトロルミネッセンス素子。
２８’．前記有機発光媒体を含有する有機薄膜層が発光層である２７’に記載の有機エレクトロルミネッセンス素子。Hereinafter, other embodiments of the present invention will be exemplified.
1 '. An organic light-emitting medium comprising a diaminopyrene derivative represented by the above formula (1) and an anthracene derivative represented by the above formula (2) (excluding those represented by the following formula (2 ′)).

(Wherein R _{1 to} R ₇ are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or An unsubstituted silyl group, a halogen atom, or a cyano group.
R _{11 to} R ₁₅ and R _{21 to} R ₂₅ are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, substituted or An unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R _{11 to} R ₁₅ and R _{21 to} R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar ₁ does not include an orthophenylene structure. )
2 '. Any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted nuclear atom having 5 to 50 nuclear atoms. The organic light-emitting medium according to 1 ′, which is a heterocyclic group.
3 '. ^One of R ¹ and R ⁸ in the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and the other is The organic luminescent medium according to 2 ′, which is a hydrogen atom.
4 '. The organic light-emitting medium according to 2 ′, wherein any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
5 '. ^One of R ¹ and R ^{8 in} the formula (2) is substituted or the organic luminescent medium according to 4 ′.
6 '. The organic light-emitting medium according to 5 ′, wherein the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms is a substituted or unsubstituted phenyl group, naphthyl group, fluorenyl group, or phenanthryl group.
7 '. The organic light-emitting medium according to any one of 1 ′ to 6 ′, wherein Ar ¹¹ in the formula (2) is a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
8 '. The organic light-emitting medium according to any one of 1 ′ to 6 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms.
9 '. The organic light-emitting medium according to 8 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are the same group.
10 '. The organic light-emitting medium according to 9 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 9-phenanthrenyl groups.
11 '. The organic light-emitting medium according to 9 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 2-naphthyl groups.
12 '. The organic light-emitting medium according to 9 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 1-naphthyl groups.
13 '. The organic light-emitting medium according to 8 ′, wherein Ar ¹¹ and Ar ¹² in the formula (2) are different groups.
14 '. The organic light emitting medium according to any one of 1 ′ to 9 ′ and 13 ′, wherein Ar ₁₁ and Ar ₁₂ in the formula (2) are each a substituted or unsubstituted phenyl group.
15 '. Ar ₁₁ and Ar ₁₂ in the formula (2) are each a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted phenyl group substituted with a heterocyclic group having 5 to 30 nuclear atoms. The organic luminescent medium according to 14 ', wherein
16 '. Ar ¹¹ and Ar ¹² in the above formula (2) are each substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted 1-naphthyl group, substituted or unsubstituted 2-naphthyl group, substituted or unsubstituted full The organic light-emitting medium according to 13 ′, which is an oranthenyl group and a substituted or unsubstituted pyrenyl group.
17 '. The organic light emission according to 13 ′, wherein one of Ar ¹¹ and Ar ¹² in the formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. Medium.
18 '. The organic light-emitting medium according to 17 ′, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 1-naphthyl group.
19 '. The organic light-emitting medium according to 17 ′, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 2-naphthyl group.
20 '. The organic light-emitting medium according to 17 ′, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted fluoranthenyl group.
21 '. The organic light-emitting medium according to 17 ′, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted pyrenyl group.
22 '. An organic light-emitting medium comprising a diaminopyrene derivative represented by the above formula (1) and an anthracene derivative represented by the above formula (2 ′).
23 '. R ^a and R ^b in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group. The organic luminescent medium according to any one of the above.
24 '. Ar ^{1 to} Ar ⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuran. The organic light-emitting medium according to any one of 1 'to 23', which is a group selected from a nyl group.
25 '. The organic light-emitting medium according to 24 ′, wherein at least one of Ar ^{1 to} Ar ⁴ in the formula (1) is a substituted or unsubstituted fluorenyl group.
26 '. R ^{21 to} R ²⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, 1 'which is a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted trimethylsilyl group, or a cyano group The organic luminescent medium in any one of -25 '.
27 '. An anode and a cathode;
Having one or more organic thin film layers between the anode and the cathode;
The organic electroluminescent element in which at least one layer of the said organic thin film layer contains the organic luminescent medium in any one of 1'-26 '.
28 '. The organic electroluminescent device according to 27 ′, wherein the organic thin film layer containing the organic light emitting medium is a light emitting layer.

  EXAMPLES Next, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not restrict | limited to these.

In the following examples and comparative examples, compounds 1-36 and compound 45-56 are the following compounds.
The following compounds were synthesized with reference to International Publication Pamphlets WO2003 / 060956 and WO2006 / 025700.

Synthesis example 1

(1) Synthesis of intermediate M-1 2-Amino-9,9-dimethylfluorene (36.6 mmol, 7.66 g), trisdibenzylideneacetone dipalladium (0.28 mmol, 0.25 g), 2, 2′-bis (diphenylphosphino) -1,1′-binaphthyl (BINAP) 0.56 mmol (0.35 g) and sodium t-butoxide 37.5 mmol (3.61 g) were added, and the system was depressurized and replaced with nitrogen. Was performed twice. Subsequently, 30 ml of toluene and 18.8 mmol (3.74 g) of 3,4,5-trimethylbromobenzene were added and reacted for 7 hours under reflux.
Insoluble matters were filtered off from the resulting reaction solution and washed with toluene. The filtrate was washed with 200 ml of a saturated aqueous sodium chloride solution, and then the organic layer was dried over magnesium sulfate. The residual oil from which the solvent was removed after filtration was purified by silica column (hexane / methylene chloride = 9/1 to 8/2) to obtain 3.7 g (yield 67%) of (M-1).

(2) Synthesis of DM17-1 In a 200 ml three-necked flask, 1,6-dibromo-3,8-di (2′-naphthyl) pyrene (BrPyr) 5.09 mmol (3.1 g), palladium acetate 0.51 mmol (0. 11 g) and 10.2 mmol (0.98 g) of sodium t-butoxide were added, the inside of the system was decompressed, and nitrogen substitution was performed twice. Next, 60 ml of toluene, 0.51 mmol (0.10 g) of tri (t-butyl) phosphine and 11.2 mmol (3.7 g) of (M-1) were added and reacted at 80 ° C. for 8 hours.
Toluene was removed from the obtained heterogeneous solution, methanol was added, and insoluble matters were filtered off. Further, washing with water and methanol was performed. This insoluble matter was recrystallized with toluene repeatedly to obtain 3.1 g of solid matter (yield 55%).
As a result of mass spectrum analysis, it was m / e = 1104 with respect to the molecular weight of 1104.54, and was the target product DM17-1.

Synthesis example 2

  In the synthesis of DM17-1 (Synthesis Example 1), 3,4,5-trimethylaniline was substituted for 2-amino-9,9-dimethylfluorene, and 3,4 was substituted for 3,4,5-trimethylbromobenzene. , 5-triethylbenzene was synthesized in the same manner. As a result of mass spectrum analysis, the product was m / e = 1040 relative to the molecular weight of 1040.60, and was the target product DM17-2.

Synthesis example 3

  In the synthesis of DM17-1 (Synthesis Example 1), 3,4,5-triethylbenzene was used instead of 3,4,5-trimethylbromobenzene, and the synthesis was performed in the same manner. As a result of mass spectrum analysis, the product was m / e = 1188 relative to the molecular weight of 1188.63, and was the target product DM17-3.

Synthesis example 4

  In the synthesis of DM17-1 (Synthesis Example 1), 3,4,5-trimethylaniline was substituted for 2-amino-9,9-dimethylfluorene, and 2-bromo was substituted for 3,4,5-trimethylbromobenzene. The compound was synthesized in the same manner using dibenzofuran. As a result of mass spectrum analysis, the product was m / e = 1136 with respect to a molecular weight of 1136.53, and was the target product DM17-4.

Example 1
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. A glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum deposition apparatus, and first, a compound A-1 having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Subsequent to the formation of the A-1 film, A-2 having a thickness of 20 nm was formed on the A-1 film. Further, on this A-2 film, the host material compound 1 of the present invention and the dopant material DM1-1 were formed in a film thickness ratio of 40: 2 with a film thickness ratio of 40: 2 to form a green light emitting layer.

On this film, Alq having a thickness of 20 nm was deposited as an electron transport layer by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode to form an organic EL light emitting device.

Examples 2-352
In Example 1, the organic EL element was similarly produced using the host material and dopant material which are shown in Tables 1-9 instead of the host material compound 1 and dopant material DM1-1.

Comparative Example 1
In Example 1, the following compound H-1 was used instead of the host material compound 1, and the dopant material DM2-4 was used instead of the dopant material DM1-1, and an organic EL device was similarly produced.

Comparative Example 2
In Example 1, an organic EL device was produced in the same manner using the compound H-1 in place of the host material compound 1 and the dopant material DM10-4 in place of the dopant material DM1-1.

Comparative Example 3
In Example 1, the following compound H-2 was used instead of the host material compound 1, and the following compound D-1 was used instead of the dopant material DM1-1 to similarly produce an organic EL device.

Comparative Example 4
In Example 1, the following compound H-3 was used instead of the host material compound 1, and the following compound D-2 was used instead of the dopant material DM1-1 to similarly produce an organic EL device.

Comparative Example 5
In Example 1, the following compound H-4 was used in place of the host material compound 1, and the compound D-2 was used in place of the dopant material DM1-1 to similarly produce an organic EL device.

Tables 1 to 9 show the luminous efficiencies of the organic EL devices obtained in Examples 1 to 352 and Comparative Examples 1 to 5 and the half lives at an initial luminance of 1000 cd / m ² .

Example 353
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. A glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and first, Compound A-3 having a film thickness of 65 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Following the formation of the A-3 film, A-2 having a film thickness of 65 nm was formed on the A-3 film. Furthermore, the host material compound 1 of the present invention and the dopant material DM2-1 were formed on the A-2 film at a film thickness ratio of 19: 1 with a film thickness of 20 nm to form a green light emitting layer.

  On this film, ET-2 having a thickness of 40 nm was deposited as an electron transport layer by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode to form an organic EL light emitting device.

Examples 354 to 408, Comparative Examples 6 to 8
In Example 353, the organic EL element was similarly produced using the host material and dopant material which are shown in Table 10 instead of the host material compound 1 and dopant material DM2-1.

Tables 10 and 11 show the light emission efficiency, the light emission wavelength, and the half life at an initial luminance of 1000 cd / m ² of the organic EL elements obtained in Examples 353 to 408 and Comparative Examples 6 to 8.

The anthracene derivative and diaminopyrene derivative of the present invention are characterized by being highly efficient and having a very long life as compared with conventionally known combinations.
In particular, in the host material, it is clear that when H-1, H-2, H-3 and the 3-substituted anthracene derivative of the present invention are compared with each other, the efficiency and life are specifically increased. This is considered to be because the emission wavelength of the host itself becomes longer by changing the anthracene substituent from two to three, and energy transfer is likely to occur with the green dopant. Further, changing the number of substituents from two to three slightly reduces the energy gap of the host material, which reduces the energy applied to the material during energization, and is considered to extend the life.
On the other hand, a diaminopyrene derivative which is a dopant material has a very long life compared to a conventionally known diaminoanthracene derivative. On the other hand, the diaminopyrene derivative tended to have a shorter wavelength than the emission wavelength required for applications such as television. However, the introduction of a fluorenyl group such as DM17-1 and DM17-3 increased the wavelength. It can be realized.

The organic EL element using the organic light emitting medium of the present invention is useful as a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.
The entire contents of the documents described in this specification are incorporated herein by reference.

Claims (27)

An organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (2).

(In formula (1), Ar ^{1 to} Ar ⁴ are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms. .
R ^{21 to} R ²⁴ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms, or a substituted or unsubstituted nuclear carbon. An aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 50 carbon atoms An oxy group, a substituted or unsubstituted arylamino group having 5 to 50 nuclear carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms, A substituted or unsubstituted silyl group, a cyano group, or a halogen atom.
n1 to n4 are each independently an integer of 0 to 5, and when each of n1 to n4 is 2 or more, R ^{21 to} R ²⁴ may be the same or different, and are connected to each other to be saturated or An unsaturated ring may be formed.
R ^a and R ^b are each independently a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear carbon atoms.

(In the formula (2), Ar ¹¹ and Ar ¹² are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms,
Any one of R ^{1 to} R ⁸ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or ^R 1 to R ⁸ other than ^R 1 to R ⁸ is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms each independently A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or An unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted carbon number It is a group selected from 2 to 50 alkoxycarbonyl groups, substituted or unsubstituted silyl groups, carboxy groups, halogen atoms, cyano groups, nitro groups and hydroxyl groups. ) Any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted nuclear atom having 5 to 50 nuclear atoms. The organic light-emitting medium according to claim 1, which is a heterocyclic group. ^One of R ¹ and R ⁸ in the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and the other is The organic light-emitting medium according to claim 2, which is a hydrogen atom. The organic light-emitting medium according to claim 2, wherein any one of R ¹ , R ² , R ⁷ and R ^{8 in} the formula (2) is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms. The organic luminescent medium according to claim 4, wherein ^one of R ¹ and R ^{8 in} the formula (2) is substituted.   The organic luminescent medium according to claim 5, wherein the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms is a substituted or unsubstituted phenyl group, naphthyl group, fluorenyl group, or phenanthryl group. The organic light-emitting medium according to claim 1, wherein Ar ¹¹ in the formula (2) is a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. The organic light-emitting medium according to any one of claims 1 to 6, wherein Ar ¹¹ and Ar ¹² in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. The organic light-emitting medium according to claim 8, wherein Ar ¹¹ and Ar ¹² in the formula (2) are the same group. The organic light-emitting medium according to claim 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 9-phenanthrenyl groups. The organic light-emitting medium according to claim 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 2-naphthyl groups. The organic light-emitting medium according to claim 9, wherein Ar ¹¹ and Ar ¹² in the formula (2) are substituted or unsubstituted 1-naphthyl groups. The organic light-emitting medium according to claim 8, wherein Ar ¹¹ and Ar ¹² in the formula (2) are different groups. The organic light-emitting medium according to claim 1, wherein Ar ¹¹ and Ar ¹² in the formula (2) are each a substituted or unsubstituted phenyl group. Ar ¹¹ and Ar ¹² in the formula (2) are each a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted phenyl group substituted with a heterocyclic group having 5 to 30 nuclear atoms. The organic light-emitting medium according to claim 14. Ar ¹¹ and Ar ¹² in the above formula (2) are each substituted or unsubstituted 9-phenanthrenyl group, substituted or unsubstituted 1-naphthyl group, substituted or unsubstituted 2-naphthyl group, substituted or unsubstituted full The organic light-emitting medium according to claim 13, which is either an oranthenyl group and a substituted or unsubstituted pyrenyl group. The organic compound according to claim 13, wherein one of Ar ¹¹ and Ar ¹² in the formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. Luminescent medium.   The organic luminescent medium according to claim 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 1-naphthyl group.   The organic light-emitting medium according to claim 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted 2-naphthyl group.   The organic light-emitting medium according to claim 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted fluoranthenyl group.   The organic luminescent medium according to claim 17, wherein the substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms is a substituted or unsubstituted pyrenyl group. R ^a and R ^b in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group. An organic light-emitting medium according to any one of the above. Ar ^{1 to} Ar ⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzofuran. The organic light-emitting medium according to claim 1, which is a group selected from a nyl group. The organic luminescent medium according to claim 23, wherein at least one of Ar ^{1 to} Ar ⁴ in the formula (1) is a substituted or unsubstituted fluorenyl group. R ^{21 to} R ²⁴ in the formula (1) are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, A substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted trimethylsilyl group, or a cyano group The organic luminescent medium in any one of 1-24. An anode and a cathode;
Having one or more organic thin film layers between the anode and the cathode;
The organic electroluminescent element in which at least one layer of the said organic thin film layer contains the organic luminescent medium in any one of Claims 1-25.   27. The organic electroluminescence device according to claim 26, wherein the organic thin film layer containing the organic light emitting medium is a light emitting layer.